Synthesis of Sulfur-Containing Heterocycles by Electrophilic Addition Reactions of Disulfur Dichloride
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Synthesis of sulfur-containing heterocycles by electrophilic addition reactions of disulfur dichloride Oleg А. Rakitin1,2* 1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia; e-mail: [email protected] 2 Nanotechnology Research and Education Center, South Ural State University, 76 Lenina Ave., Chelyabinsk 454080, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 837–847
Submitted April 30, 2020 Accepted May 18, 2020
This review compiles and summarizes approaches to the preparation of heterocyclic systems containing sulfur atoms based on the reactions of disulfur dichloride which acts as an electrophilic reagent. It is shown that as a result of these transformations heterocycles with different numbers of sulfur atoms can be synthesized: 1,2,5-thiadiazoles, 1,2- and 1,4-thiazines, 1,2-dithiols, 1,2,3-dithiazoles, 1,2,3,4,5-pentathiepines, 1,2,3,4,5,6,7-heptathiocanes, and many others. The yields of the products of these reactions depend to a significant extent on the ratio of the reactants, the nature of the solvent, the base used, and the temperature. The exceptional role of disulfur dichloride in the synthesis of various sulfur-containing heterocycles is shown. Keywords: disulfur dichloride, sulfur-containing heterocycles, cyclization, electrophilic addition.
Sulfur-containing heterocyclic compounds are one of the most studied classes of heterocycles. This is due to the importance of the role of sulfur not only in the vital processes of all organisms, including humans, and the associated biological activity, but also the promising nature of materials based on sulfur-containing heterocycles in various fields of science and technology. Therefore, the problem of introducing sulfur atoms into organic molecules, including with the formation of heterocyclic rings, is urgent. A large number of sulfurating agents are known that can introduce sulfur atoms with various oxidation states. Sulfur chlorides, in particular the most 0009-3122/20/56(7)-0837©2020 Springer Science+Business Media, LLC
stable and commercially available disulfur dichloride (S2Cl2), occupy an important place among them.1–3 The main feature of S2Cl2 is its varied reactivity, which determines both its positive and negative properties. S2Cl2 exhibits the properties of a sulfurating, chlorinating, oxidizing, and even dehydrating agent. Often, all of these multiple reactivities of S2Cl2 occur simultaneously, resulting in difficult-to-separate product mixtures. The sulfurating ability of S2Cl2 is evidently manifested in the addition of the electrophilic species +S–S–Cl, and the products of the first step of reactions with S2Cl2 are presumably chlorodithio derivatives 1, which, although not 837
Chemistry of Heterocyclic Compounds 2020, 56(7), 837–847
isolated in this reaction, are presumed to be formed in almost every description of such a transformation (Scheme 1).1–3 Numerous attempts have been made to replace the chlorine atoms in S2Cl2 with a carbon, oxygen,
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